11. Academy of Country Music’s New Artists’ Party – 2007
Swift performed at the Academy of Country Music’s New Artists’ Party in 2007 in this lacy aqua dress with a pair of coordinating cowboy boots. She posed for photos with her friend Kellie Pickler, who she would later to team up with for the song “Best Days of Your Life.”
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10. Life Magazine’s 10th Annual Young Hollywood Awards – 2008
At Life Magazine’s 10th Annual Young Hollywood Awards, the “Tim McGraw” singer received the Superstar of Tomorrow Award. She was the first musician in history to receive this. She certainly did end up becoming the superstar of tomorrow! More than a decade later and she’s still here and more popular than ever!
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9. Clive Davis Pre-Grammy Party – 2008
Taylor was a guest at the legendary Clive Davis Pre-Grammy Party in 2008. She donned this cream-colored dress that was cute but super girly. Her style is definitely different now and if she doesn’t want to pose on a red carpet, she doesn’t! Back then, however, she did not have much of a choice. She was still trying to get her name out there.
8. 42nd Annual Academy of Country Music Awards – 2007
The “Teardrops on My Guitar” singer performed at the 42nd Annual Academy Of Country Music Awards during the all-star jam. She rocked this strapless dress, which featured some feathered embellishments on the skirt, with a pair of her signature cowboy boots.
Ethan Miller/ACMA/Getty Images for ACMA